4-Fluorobenzoyl chloride → HCID 178525712, compound

HRID 2209393Notes

Reaction equation

HRID 2209393 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[O:11]1[CH2:15][CH2:14][O:13][CH:12]1[CH2:16][CH2:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([C@H:24]2[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]2)[CH2:20][CH2:19]1>N1C=CC=CC=1>[O:11]1[CH2:15][CH2:14][O:13][CH:12]1[CH2:16][CH2:17][C@H:18]1[CH2:19][CH2:20][C@H:21]([C@H:24]2[CH2:29][CH2:28][C@H:27]([O:30][C:6](=[O:7])[C:5]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:26][CH2:25]2)[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 178521563HCID 178521563, compound

Product 1

HCID 178525712HCID 178525712, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.7 g of 4-fluorobenzoyl chloride in 5 ml of pyridine is treated with 2.8 g of trans-4-[trans-4-[2-(1,3-dioxolan-2-yl)ethyl]cyclohexyl]cyclohexanol (prepared according to Example 3) and stirred at room temperature for 12 hours. Thereafter, the reaction mixture is poured on to ice-water and extracted three times with diethyl ether. The organic phases are washed in succession with saturated sodium hydrogen carbonate solution, with 10 percent hydrochloric acid, with saturated sodium hydrogen carbonate solution and with water, then dried over magnesium sulfate, filtered and concentrated. Chromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gives 4-fluorobenzoic acid trans-4-[trans-4-[2-(1,3-dioxolan-2-yl)ethyl]cyclohexyl]cyclohexyl ester.

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe organic phases are washed in succession with saturated sodium hydrogen carbonate solution, with 10 percent hydrochloric acid, with saturated sodium hydrogen carbonate solution and with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97)

Sources & evidence

ORD record
ord-7cf3be6f262b468ba220acc92580ba93
Source dataset
uspto-grants-1995_10
Patent number
US05454974

Reaction notes

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